Exchange 2010 Secure Email

Business partner requiring secure email communication. Not a problem, or so I thought. Company has Exchange 2010 with a Barracuda Spam/Virus Firewall filtering inbound mail only. Outbound mail is sent directly from Exchange. fqdn for mail is pointing to Barracuda.

Mail flow is working fine. No problems AFAIK.

I have purchased cert for securing the email. It is using the fqdn of mail. In talking with the tech support at Barracuda, the Barracuda sends the email up to their service for encryption. End user would receive email that encrypted email is available by clicking on link. An additional step or two required by the end user. Not really the way that I wanted it to work.

Not sure if the barracuda will pass encrypted email. I could have the email for the biz partner domain to bypass filtering.

I was planning on configuring encrypted email on the exchange server. Then I remembered that the Barracuda was in the path of the mail flow (inbound only).

Possible work around.

Adding another MX record to bypass the Barracuda, though it would open up email traffic from all servers.

Use a different public IP address for exchange encrypted mail. Filter at the firewall to allow only smtp traffic from biz partner email servers. Setup receive connector with fqdn of mail to allow inbound email.

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Originally my thought was to use Exchange to do the encryption/decryption. Since the barracuda is in the path of the mail flow, I will probably use it to start. This may be the easiest path. Hopefully I can get some time to work it out in a lab. Of course I may never get the chance due to work load.

I am waiting on the other party to contact me, so we can test operation.

Thanks everyone for the ideas. I ended up using the barracuda to handle the email encryption. Some of their techs were misleading in the information given to me. So basically email is encrypted between the client and Exchange, and then between Exchange and the barracuda. Then the barracuda handles the encryption with outside email servers. I finally found the correct info thru one of their techs. Also, the ssl certs were not recognized by the barracuda. Once this was corrected, it worked fine. Except for the issue with the cisco firewall and its fixup protocol for esmtp. I had to disable it altogether.

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